Can you be a little more clear in what you need help with? For example, if
you are going to ask how to setup PostFix to offer secure POP/SMTP, I'm
going to say you should find a support group that supports your flavor of
Unix/Linux and PostFix since this group only support Microsoft Outlook.
If you are asking how to I ensure that Microsoft Outlook/Operating System
can ensure the validity of a certificate, I will ask... Is your site using a
server certificate issued by a 3rd party (e.g. Thawte, Verisign, .etc) or an
Internal Certificate Authority (e.g. a self signed).
If the certificate was issued by a 3rd party, you don't have to do anything
on the client side (other than configure the outlook account to use ssl) to
verify the certicate up the chain since 3rd party vendor's signing root
certificates authorities are already installed on Windows.
If you are creating a self-signed/issued certificate, then you need to
install a copy of the internal root certificate on your windows box. This
can be accomplished through Internet Explorer's internet options. (Tools |
Internet Options | Content tab | Certificates)